Chronic Sailing

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Chronic Sailing Annapolis Sailboat Charters;
ASA Affiliate Sailing School;
Captain Services &
Professional Yacht Delivery
(5)

10/16/2026

We are at the this weekend and you need to come find us.

Chronic Sailing is set up deep in Ego Alley right at the entrance near Chop Tank with a Neel 52 trimaran. Come say hi, check out the boat, and talk to the team about charters, management, and what we have going on heading into the off season.

Saturday and Sunday. Annapolis Sailboat Show. Come find us. ⛵

Thanksgiving Saturday. You’ve eaten your weight in stuffing, your cousins are still at the house, and the group chat is ...
10/16/2026

Thanksgiving Saturday. You’ve eaten your weight in stuffing, your cousins are still at the house, and the group chat is doing the “what are we doing tonight” thing for the third year in a row.

We fixed it.

WINTER WONDERJAM at Dark Horse:
• 7 live bands, noon to 7
• A holiday vendor market, so you can buy actual gifts instead of panic-ordering on the 23rd
• All proceeds goes to Chronic Cares, so you can feel good about it while standing near a speaker

Bring the cousins. Bring the one friend who’s “not really a live music person.” They’ll be fine.

Vendors, want in? Email [email protected] and we’ll get you a table.

Lineup coming soon. Save this post, you’re gonna want it.
📍 985 Bay Ridge Rd, Annapolis
🕛 12 to 7 PM
📅 Sat Nov 28

10/15/2026

We just bought J World!

Party tonight at 7pm! 213 Eastern Ave, Annapolis. Come celebrate with us.

Chronic Sailing Tunesday Pop-Up at Stan & Joe's Riverside
09/25/2026

Chronic Sailing
Tunesday Pop-Up
at Stan & Joe's Riverside

09/18/2026

Shawn and Ron said everything you need to know. We are just here to make sure you do not miss it.

Baygrass Music Festival is this weekend. Saturday and Sunday. And it kicks off Friday night at Maryland Hall at 7pm with Jammy Buffet, a Jimmy Buffett cover band that sounds exactly as good as it does, and Cumberland Honey. Tickets are $20 in advance and more at the door so get them now.

Saturday and Sunday is the full festival and you already know the lineup. What you might not know is that the Chronic Crew gets 15% off.

Use code BGFAM15 at checkout. That is B-G-F-A-M-1-5.

This is the only festival we support the way we do and it is for a reason. Baygrass gets it. The bay, the music, the community. All of it.

Come out. 🎶⛵

📅 Friday — Maryland Hall, 7pm. Doors open. $20 advance.
📅 Saturday and Sunday — Baygrass Music Festival. Full lineup. Full weekend.
🎟️ 15% off with code BGFAM15

Annapolis Baygrass Music Festival

09/05/2026

🚨New song debut: “Beeswax ft Big SLOP” live from the Chronic Sailing Catamaran on Back Creek Annapolis. If SLOP is MC on the floating stage concert, you best believe I’m gonna request he spit a few stanzas about vintage cucumbers. 🥒 “It might be time to refresh your philosophy if you thought your train of thought right off the rails, liberate yourself from the hypocrisy, inhale, exhale…” Video by Casey V. Bougie bootleg field recording by 3 Eyed Ghost Cat Slop (Spittin' Lyrics On Point)
⚓️

06/26/2026

The bay is calling and honestly it would be rude not to go.

Charter season is here and Sea Dancer is ready. Day trips, sunset cruises, or a full day out on the Chesapeake with your whole crew. Bring the food, bring the drinks, and let us handle the rest.

Meet Sea Dancer:

🛥️ Meridian 541 Sedan power yacht
👥 Up to 13 guests
🛏️ 2 private cabins, sleeps 4-6
🚿 2 heads
🛋️ Open salon with full lounge and galley
🌅 Expansive flybridge with views for days
⚓ Multiple deck zones for lounging, dining, and swimming

Link in bio to book. 🌅⛵

Address

7082 Bembe Beach Road, #204
Annapolis, MD
21403

Telephone

+14433339113

Website

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